Compound, refractive index enhancer, and polymer

Abstract

To provide a compound capable of offering a high-refractive-index resin material.SOLUTION: The compound of the present invention is: a compound represented by the chemical formula (1) in the figure; a tautomer or stereoisomer thereof; or a salt of them. In the formula: A is a single bond, a divalent hydrocarbon group, or a sulfonyl group; R1 and R2 are each a linear or alicyclic hydrocarbon group or an aralkyl group having 1 to 12 carbon atoms; and X1 and X2 are each a hydrogen atom or a polymerizable functional group.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a compound, a refractive index enhancer, and a polymer. [Background technology]

[0002] Various biphenols and bisphenols have been studied. Furthermore, Patent Document 1 proposes introducing a polymerizable functional group into the biphenols or bisphenols and using them as high refractive index resin materials for optical articles such as epoxy resins, polyester resins, polyurethane resins, polybutyral resins, liquid crystal display panels, color filters, eyeglass lenses, Fresnel lenses, lenticular lenses, TFT prism lens sheets, optical fibers, and optical disks. The compound represented by chemical formula (1) in Patent Document 1 is a novel polymerizable monomer useful as a high refractive index resin material for optical articles such as liquid crystal display panels, color filters, eyeglass lenses, Fresnel lenses, lenticular lenses, TFT prism lens sheets, optical fibers, and optical disks. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] WO2016 / 002607A1 Summary of the Invention [Problem to be solved by the invention]

[0004] However, in applications such as those described in Patent Document 1, high refractive index resin materials are being made thinner, and there is a demand for resins with even higher refractive indexes.

[0005] Therefore, an object of the present invention is to provide a compound, a refractive index enhancer, and a polymer that can provide a resin material having a high refractive index. [Means for solving the problem]

[0006] In order to achieve the above object, the compound of the present invention is a compound represented by the following chemical formula (1), a tautomer or stereoisomer thereof, or a salt thereof.

[0007] [ka]

[0008] In the above chemical formula (1), A is a single bond, a divalent hydrocarbon group, or a sulfonyl group, and one or more hydrogen atoms in the divalent hydrocarbon group are each independently optionally substituted with a methyl group or a phenyl group; R 1 and R 2 each represents a linear or alicyclic hydrocarbon group having 1 to 12 carbon atoms or an aralkyl group; R 1 and R 2 may be the same or different, X 1 and X 2 are each a hydrogen atom or a polymerizable functional group, and may be the same or different.

[0009] The refractive index enhancer of the present invention is a refractive index enhancer containing the compound of the present invention, a tautomer or stereoisomer thereof, or a salt thereof.

[0010] The polymer of the present invention is a polymer of a monomer component containing the compound of the present invention, a tautomer or stereoisomer thereof, or a salt thereof. Effect of the Invention

[0011] According to the present invention, it is possible to provide a compound, a refractive index enhancer, and a polymer capable of providing a resin material having a high refractive index. [Brief description of the drawings]

[0012] [Figure 1] FIG. 1 shows the results of IR analysis of the compound obtained in Example 1. [Diagram 2]FIG. 2 shows the results of IR analysis of the compound obtained in Example 2. [Diagram 3] FIG. 3 shows the results of IR analysis of the compound obtained in Example 3. [Figure 4] FIG. 4 shows the results of IR analysis of the compound obtained in Example 4. [Diagram 5] FIG. 5 shows the results of IR analysis of the compound obtained in Example 5. [Figure 6] FIG. 6 shows the results of IR analysis of the compound obtained in Example 6. [Figure 7] FIG. 7 shows the results of IR analysis of the compound obtained in Example 7. [Figure 8] FIG. 8 shows the results of IR analysis of the compound obtained in Example 8. [Figure 9] FIG. 9 shows the results of IR analysis of the compound obtained in Example 9. [Figure 10] FIG. 10 shows the results of IR analysis of the compound obtained in Example 10. [Figure 11] FIG. 11 shows the results of IR analysis of the compound obtained in Example 11. [Figure 12] FIG. 12 shows the results of IR analysis of the compound obtained in Example 12. [Figure 13] FIG. 13 shows the results of IR analysis of the compound obtained in Example 13. [Figure 14] FIG. 14 shows the results of IR analysis of the compound obtained in Example 14. [Figure 15] FIG. 15 shows the results of IR analysis of the compound obtained in Example 15. [Figure 16] FIG. 16 shows the results of IR analysis of the compound obtained in Example 16. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0013] Next, the present invention will be described in more detail with reference to examples, but the present invention is not limited to the following description in any way.

[0014] In the present invention, when a compound (e.g., a compound represented by the above chemical formula (1)) has isomers such as tautomers or stereoisomers (e.g., geometric isomers, conformational isomers, and optical isomers), any of the isomers can be used in the present invention, unless otherwise specified. Furthermore, when a compound can form a salt, the salt can also be used in the present invention, unless otherwise specified. The salt may be an acid addition salt or a base addition salt. Furthermore, the acid that forms the acid addition salt may be an inorganic acid or an organic acid, and the base that forms the base addition salt may be an inorganic base or an organic base. The inorganic acid is not particularly limited, but examples thereof include sulfuric acid, phosphoric acid, hydrofluoric acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, hypofluorite acid, hypochlorous acid, hypobromite acid, hypoiodite acid, fluorite acid, chlorous acid, bromite acid, iodite acid, fluorine acid, chlorine acid, bromine acid, iodine acid, perfluorine acid, perchloric acid, perbromine acid, and periodic acid. The organic acid is also not particularly limited, but examples thereof include p-toluenesulfonic acid, methanesulfonic acid, oxalic acid, p-bromobenzenesulfonic acid, carbonic acid, succinic acid, citric acid, benzoic acid, and acetic acid. The inorganic base is not particularly limited, but examples thereof include ammonium hydroxide, alkali metal hydroxide, alkaline earth metal hydroxide, carbonate, and hydrogen carbonate, and more specifically, examples thereof include sodium hydroxide, potassium hydroxide, potassium carbonate, sodium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, calcium hydroxide, and calcium carbonate. The organic base is not particularly limited, and examples thereof include ethanolamine, triethylamine, tris(hydroxymethyl)aminomethane, etc. The method for producing these salts is also not particularly limited, and they can be produced, for example, by a method in which the above-mentioned acid or base is appropriately added to the above-mentioned compound by a known method.

[0015] In the present invention, a chain-like substituent (e.g., a hydrocarbon group such as an alkyl group, an alkylene group, or an unsaturated aliphatic hydrocarbon group) may be linear or branched unless otherwise specified, and the number of carbon atoms is not particularly limited, and may be, for example, 1 to 40, 1 to 32, 1 to 24, 1 to 18, 1 to 12, 1 to 6, 1 to 4, or 1 to 2 (2 or more in the case of an unsaturated hydrocarbon group). In the present invention, the number of ring members (the number of atoms constituting the ring) of a cyclic group (e.g., an aryl group, a heteroaryl group, etc.) is not particularly limited, and may be, for example, 5 to 32, 5 to 24, 6 to 18, 6 to 12, or 6 to 10. In addition, when an isomer exists in a substituent, etc., any isomer may be used unless otherwise specified, and for example, when simply referring to a "naphthyl group", it may be a 1-naphthyl group or a 2-naphthyl group.

[0016] [1. Compound of the present invention and its production method] As described above, the compound of the present invention is a compound represented by the above chemical formula (1), a tautomer or stereoisomer thereof, or a salt thereof. In addition, as shown in the above chemical formula (1), the compound of the present invention is a compound having a polymerizable functional group, X 1 and X 2 Since the compound of the present invention contains the compound having a high refractive index, it can be polymerized to form a polymer. The compound of the present invention itself has a high refractive index, and therefore can provide a resin material having a high refractive index by polymerization.

[0017] In the present invention, the compound represented by the chemical formula (1) may be, for example, a compound represented by the following chemical formulas (101) to (104), (111) to (113), (121) to (124), (131), (141), (151) to (154), or (161).

[0018] [ka]

[0019] [ka]

[0020] [ka]

[0021] [ka]

[0022] [ka]

[0023] [ka]

[0024] A method for synthesizing (producing) the compound represented by the above chemical formula (1) will be described below with reference to an example.

[0025] In the above chemical formula (1), A is a single bond, a divalent hydrocarbon group, or a sulfonyl group, and R 1 and R 2 The compound in which is a benzyl group can be synthesized (produced) using, for example, a compound represented by the following chemical formula (6) (hereinafter also referred to as "Bz-OPP") as a raw material.

[0026] [ka]

[0027] "Bz-OPP" can be synthesized, for example, by the method described in The Journal of Organic Chemistry, 1970, Vol. 35, No. 1, pp. 57-62, but is not limited to this method and may be synthesized by any other method.

[0028] In the above chemical formula (1), A is a single bond, a divalent hydrocarbon group, or a sulfonyl group, and R 1 and R 2The compound in which is an α-methylbenzyl group can be synthesized (produced) using, for example, a compound represented by the following chemical formula (7) (hereinafter also referred to as “St-OPP”) as a raw material.

[0029] [ka]

[0030] "St-OPP" can be synthesized, for example, by using 2-(1-phenylethyl)phenol as a starting material and further using styrene instead of cyclohexene in the method described in JP 2009-269868 A, but is not limited to this method and may be synthesized by any other method.

[0031] In the above chemical formula (1), A is a single bond, a divalent hydrocarbon group, or a sulfonyl group, and R 1 and R 2 A compound in which is a cyclohexyl group can be synthesized (produced) using, for example, a compound represented by the following chemical formula (8) (hereinafter also referred to as "CPP") as a raw material.

[0032] [ka]

[0033] The compound in which A is a single bond in the above chemical formula (1) can be synthesized, for example, by the method described in Bull. Korean Chem. Soc. 1999, Vol. 20, No. 4, pp. 469-472, using the compounds represented by the above chemical formulas (6) to (8) as raw materials, but is not limited to this method and may be synthesized by other methods. The compound in which A is a single bond in the above chemical formula (1) synthesized by the above method is, for example, a compound represented by the following chemical formula (9). In the following chemical formula (9), R 1 and R 2 is R in the above chemical formula (1). 1 and R 2The compounds represented by the above chemical formula (1) in which A is a single bond are, for example, the compounds represented by the above chemical formulae (101) to (103). [ka]

[0034] The compound in which A is a methylene group in the above chemical formula (1) can be synthesized, for example, by the method described in European Polymer Journal, 1970, Vol. 6, pp. 1339-1346, using the compounds represented by the above chemical formulas (6) to (8) as raw materials, but is not limited to this method and may be synthesized by other methods. The compound in which A is a methylene group in the above chemical formula (1) synthesized by the above method is, for example, a compound represented by the following chemical formula (10). In the following chemical formula (10), R 1 and R 2 is R in the above chemical formula (1). 1 and R 2 The compound represented by the above chemical formula (1) in which A is a methylene group is, for example, a compound represented by the above chemical formula (104). [ka]

[0035] In the chemical formula (1), A is, as described above, a single bond, a divalent hydrocarbon group, or a sulfonyl group, and one or more hydrogen atoms in the divalent hydrocarbon group may be independently substituted with a methyl group or a phenyl group. In A, the divalent chain-like hydrocarbon group may be linear or branched, saturated or unsaturated. Examples of the divalent chain-like hydrocarbon group include linear or branched alkylene groups, linear or branched alkenylene groups, and linear or branched alkynylene groups. Examples of the divalent chain-like hydrocarbon group include divalent hydrocarbon groups having 1 to 4 carbon atoms (e.g., methylene group, ethylene group, propylene group, etc.), divalent hydrocarbon groups having 2 to 5 carbon atoms to which one methyl is added (e.g., methylmethylene group, etc.), and divalent hydrocarbon groups having 3 to 6 carbon atoms to which two methyls are added (dimethylmethylene group, etc.), and a methylene group or a dimethylmethylene group is particularly preferred.

[0036] In A in the chemical formula (1), as described above, one or more hydrogen atoms in the divalent hydrocarbon group may be independently substituted with a methyl group or a phenyl group. The A may be, for example, a divalent hydrocarbon group having 7 to 10 carbon atoms to which one phenyl group is added (i.e., one hydrogen atom is substituted with a phenyl group). An example of the divalent hydrocarbon group having 7 to 10 carbon atoms to which one phenyl group is added is a phenylmethylene group. The A may be, for example, a divalent hydrocarbon group having 13 to 16 carbon atoms to which two phenyl groups are added (i.e., two hydrogen atoms are substituted with phenyl groups). An example of the divalent hydrocarbon group having 13 to 16 carbon atoms to which two phenyl groups are added is a diphenylmethylene group. The A may be, for example, a divalent hydrocarbon group having 8 to 11 carbon atoms to which a methyl group and a phenyl group have been added (i.e., one or more hydrogen atoms have been substituted with a methyl group and one or more hydrogen atoms have been substituted with a phenyl group). Examples of the divalent hydrocarbon group having 8 to 11 carbon atoms to which a methyl group and a phenyl group have been added include a methylphenylmethylene group. In the A, as the group in which one or more hydrogen atoms in the divalent chain-like hydrocarbon group have been substituted with a methyl group or a phenyl group, a phenylmethylene group or a diphenylmethylene group is particularly preferred.

[0037] As described above, A in the chemical formula (1) may be a divalent alicyclic hydrocarbon group, for example, a cyclohexylene group.

[0038] In the above chemical formula (1), A is preferably a single bond or a methylene group. As described above, a sulfonyl group can also be selected as A in the above chemical formula (1).

[0039] The polymerizable functional group X in the above chemical formula (1) 1 and X 2 As described above, may be the same or different, but are preferably the same.

[0040] The polymerizable functional group X in the above chemical formula (1)1 and X 2 is represented by the following chemical formula (2), the compound represented by the chemical formula (1) can be synthesized, for example, by the method represented by the following scheme 1 or the method represented by the following scheme 2. The method represented by the following scheme 1 or the method represented by the following scheme 2 is a method of reacting a compound represented by the chemical formula (9) or the chemical formula (10) with halovinyl or haloallyl. The reaction conditions are not particularly limited, and for example, the reaction may be performed without a solvent or in an organic solvent, or may be performed using a catalyst or may be performed without a catalyst.

[0041] [ka]

[0042] [ka]

[0043] [ka]

[0044] The halovinyl or haloallyl is not particularly limited, but examples thereof include vinyl chloride, vinyl bromide, allyl chloride, and allyl bromide.

[0045] The total amount of the halovinyl or haloallyl used is not particularly limited, but is preferably 1 to 6 times, and more preferably 2 to 4 times, the molar amount of the compound represented by the chemical formula (9) or the chemical formula (10).

[0046] The polymerizable functional group X in the above chemical formula (1) 1 and X 2is represented by the following chemical formula (3), the compound represented by the chemical formula (1) can be synthesized, for example, by the method represented by the following scheme 3 or the method represented by the following scheme 4. The method represented by the following scheme 3 or the method represented by the following scheme 4 is a method of reacting a compound represented by the chemical formula (9) or the chemical formula (10) with epihalohydrin. The reaction conditions are not particularly limited, and for example, the reaction may be performed without a solvent or in an organic solvent, and may be performed using a catalyst or without a catalyst.

[0047] [ka]

[0048] [ka]

[0049] [ka]

[0050] The epihalohydrin is not particularly limited, but examples thereof include epichlorohydrin and epibromohydrin.

[0051] The total amount of the epihalohydrin used is not particularly limited, but is preferably 1 to 12 times the molar amount of the compound represented by the chemical formula (9) or the chemical formula (10), and more preferably 2 to 10 times the molar amount.

[0052] In the steps of Schemes 3 and 4, the reaction temperature is not particularly limited, but is preferably -10°C to 150°C. If the reaction temperature is too high, by-products may be generated, and if the reaction temperature is too low, the reaction time is too long. The reaction temperature is more preferably 20°C to 130°C. The reaction time of the steps is not particularly limited and can be adjusted depending on the reaction temperature, but is preferably 1 to 15 hours.

[0053] The polymerizable functional group X in the above chemical formula (1) 1 and X 2 is represented by the following chemical formula (4), the compound represented by the chemical formula (1) can be synthesized, for example, by the method represented by the following scheme 5 or the method represented by the following scheme 6. The method represented by the following scheme 5 or the method represented by the following scheme 6 is a method of reacting a compound represented by the chemical formula (9) or the chemical formula (10) with one or more selected from the group consisting of ethylene oxide, ethylene carbonate, propylene oxide, and propylene carbonate. The reaction conditions are not particularly limited, and for example, the reaction may be performed without a solvent or in an organic solvent, or may be performed using a catalyst or may be performed without a catalyst.

[0054] [ka]

[0055] [ka]

[0056] [ka]

[0057] The total amount of the ethylene oxide, ethylene carbonate, propylene oxide, and propylene carbonate used is not particularly limited, but is preferably, for example, 1 to 3 times by mole when m is 1, 3 to 5 times by mole when m is 2, and 5 to 6 times by mole when m is 3, relative to the compound represented by the chemical formula (9) or the chemical formula (10).

[0058] In the steps of Schemes 5 and 6, the reaction temperature is not particularly limited, but is preferably -20°C to 200°C. If the reaction temperature is too high, by-products may be generated, and if the reaction temperature is too low, the reaction time is too long. The reaction temperature is more preferably 0°C to 180°C. The reaction time of the steps is not particularly limited, and is preferably adjusted according to the reaction temperature, but is preferably 1 to 18 hours.

[0059] The polymerizable functional group X in the above chemical formula (1) 1 and X 2 is represented by the following chemical formula (5), and in the following chemical formula (5), l is 0, the compound represented by the chemical formula (1) can be synthesized, for example, by the method represented by the following scheme 7 or the method represented by the following scheme 8. The method represented by the following scheme 7 or the method represented by the following scheme 8 is a method of reacting a compound represented by the chemical formula (9) or the chemical formula (10) with one or more selected from the group consisting of (meth)acrylic acid, (meth)acrylic acid chloride, and di(meth)acrylic acid anhydride. The reaction conditions are not particularly limited, and for example, the reaction may be performed without a solvent or in an organic solvent, may be performed using a catalyst, or may be performed without a catalyst. In the present invention, "(meth)acrylic" means "at least one of acrylic and methacrylic". For example, "(meth)acrylic acid" means "at least one of acrylic acid and methacrylic acid". "(meth)acrylic acid chloride" means "at least one of acrylic acid chloride and methacrylic acid chloride". "Di(meth)acrylic anhydride" refers to "at least one of diacrylic anhydride and dimethacrylic anhydride."

[0060] [ka]

[0061] [ka]

[0062] [ka]

[0063] The total amount of the (meth)acrylic acid, (meth)acrylic acid chloride, or di(meth)acrylic anhydride used is not particularly limited, but is preferably 1 to 6 times, and more preferably 2 to 4 times, the molar amount of the compound represented by the chemical formula (9) or the chemical formula (10).

[0064] In the steps of Schemes 7 and 8, the reaction temperature is not particularly limited, but is preferably -20°C to 100°C. If the reaction temperature is too high, by-products may be generated, and if the reaction temperature is too low, the reaction time is too long. The reaction temperature is more preferably -10°C to 40°C. The reaction time of the steps is not particularly limited, and is preferably adjusted according to the reaction temperature, but is preferably 1 to 8 hours.

[0065] The polymerizable functional group X in the above chemical formula (1) 1 and X 2 is represented by the following chemical formula (5), and in the following chemical formula (5), l is 1 to 3, the compound represented by the chemical formula (1) can be synthesized, for example, by the method represented by the following scheme 9 or the method represented by the following scheme 10. The method represented by the following scheme 9 or the method represented by the following scheme 10 is a method in which the compound (9)-3 is synthesized by the above scheme 5, or the compound (10)-3 is synthesized by the above scheme 6, and then the compound (9)-3 or the compound (10)-3 is reacted with one or more selected from the group consisting of (meth)acrylic acid, (meth)acrylic acid chloride, and di(meth)acrylic anhydride. The reaction conditions are not particularly limited, and for example, the reaction may be performed without a solvent or in an organic solvent, or may be performed using a catalyst or may be performed without a catalyst.

[0066] [ka]

[0067] [ka]

[0068] [ka]

[0069] In the above-mentioned scheme 9 or 10, the total amount of (meth)acrylic acid, (meth)acrylic acid chloride, or di(meth)acrylic anhydride used is not particularly limited, but is preferably 1 to 6 times by mole, and more preferably 2 to 4 times by mole, relative to the compound represented by the above-mentioned chemical formula (9) or the above-mentioned chemical formula (10).

[0070] In the scheme 9 or 10, the reaction temperature of the step of reacting the compound (9)-3 or the compound (10)-3 with one or more selected from the group consisting of (meth)acrylic acid, (meth)acrylic acid chloride, or di(meth)acrylic anhydride is not particularly limited, but is preferably -20°C to 200°C. If the reaction temperature is too high, by-products may be generated, and if the reaction temperature is too low, the reaction time is too long. The reaction temperature is more preferably -10°C to 140°C. The reaction time of the step is not particularly limited, and is preferably adjusted depending on the reaction temperature, but is preferably 1 to 20 hours.

[0071] When a solvent is used in the reactions of the schemes 1 to 10, the solvent is not particularly limited, but examples thereof include esters such as methyl acetate, ethyl acetate, phenyl acetate, and benzyl acetate; halogenated hydrocarbons such as dichloromethane and trichloromethane; ketones such as acetone and methyl isobutyl ketone; ethers such as diethyl ether and tetrahydrofuran; aromatic hydrocarbons such as benzene, toluene, and xylene; and amides such as N,N-dimethylformamide (DMF) and N,N-dimethylacetamide (DMAc). The organic solvents may be used alone or in combination of two or more kinds.

[0072] When a catalyst is used in the reactions of Schemes 1 to 10, the catalyst is not particularly limited, and examples thereof include metal hydroxides such as sodium hydroxide and potassium hydroxide, basic compounds such as tetramethylammonium chloride and benzyltriethylammonium chloride, inorganic acids such as hydrochloric acid and sulfuric acid, organic acids such as acetic acid, paratoluenesulfonic acid and methanesulfonic acid, inorganic bases such as carbonates or hydrogencarbonates such as sodium carbonate, sodium hydrogencarbonate, potassium carbonate and potassium hydrogencarbonate, and amines such as monoethylamine, diethylamine and triethylamine. The catalyst may be used alone or in combination of two or more.

[0073] In the reactions of Schemes 1 to 10, after the reaction of each step is completed, for example, taking into consideration the physical properties of each compound, the type and amount of the raw material and organic solvent used, a post-treatment may be carried out as necessary by a known method, and each compound may be taken out. Specifically, for example, post-treatment operations such as filtration, washing, extraction, pH adjustment, dehydration, and concentration may be carried out alone or in combination of two or more types as appropriate, and each compound may be taken out by concentration, crystallization, reprecipitation, column chromatography, etc. Furthermore, each of the taken out compounds may be purified by carrying out operations such as crystallization, reprecipitation, column chromatography, extraction, stirring and washing of crystals with a solvent alone or in combination of two or more types once or more as necessary.

[0074] Since the compound of the present invention has a polymerizable functional group, it is possible to produce a resin material formed by the polymer by polymerizing the compound of the present invention. The polymer may be a polymer of the compound of the present invention alone or a copolymer with other monomer components. The conditions of the polymerization reaction (reaction temperature, reaction time, etc.) are not particularly limited, and may be appropriately set with reference to known polymerization reaction conditions, for example, depending on the type of polymerizable functional group possessed by the compound of the present invention. The polymerization reaction may be carried out, for example, by reacting the compound of the present invention in the presence of the compound of the present invention or other compounds (such as the other monomer components) and optionally adding a solvent, catalyst, etc. EXAMPLES

[0075] Examples (including synthesis examples) of the present invention will be described below together with comparative examples. However, the present invention is not limited to the following examples. In the following examples, "parts" means "parts by mass" unless otherwise specified, and "%" means "% by mass" unless otherwise specified.

[0076] The physical properties shown in the following Examples and Reference Examples were measured by the following methods.

[0077] 1 H-NMR was recorded on a JEOL Ltd. nuclear magnetic resonance (NMR) JNM-ECZ400 (trade name) instrument using trimethylsilane (TMS) as an internal standard and deuterated chloroform (CDCl 3 ) as a solvent.

[0078] The melting point was measured using a differential scanning calorimeter (DSC) DSC-50 (trade name) manufactured by Shimadzu Corporation.

[0079] The average molecular weight was measured using a high performance liquid chromatograph (HPLC) (LC-20AD (product name)) manufactured by Shimadzu Corporation, and was calculated as a polystyrene standard equivalent value by gel permeation chromatography (GPC).

[0080] The infrared absorption was measured by an ATR method using an infrared spectrophotometer (IR) IRAffinity-1S (product name) manufactured by Shimadzu Corporation.

[0081] The refractive index was measured as follows. First, a compound to be measured for the refractive index was dissolved in 1-bromonaphthalene or N-methyl-2-pyrrolidone (hereinafter also referred to as "NMP") to prepare a 5% by weight or 10% by weight solution. Next, the refractive index of each adjusted solution and that of the solvent 1-bromonaphthalene or NMP as a control were measured using a DR-2M (trade name) device manufactured by Atago Co., Ltd. An approximation line was derived from the three measured values ​​obtained by the measurement. The 100% by weight value of each compound to be measured for the refractive index was read from the approximation line and used as the refractive index value.

[0082] [Example 1] In a 1000mL four-neck flask, 130.2g (0.50mol) of Bz-OPP, 260.4g of benzonitrile, and 15.3g of copper(I) chloride were charged, and the mixture was heated to about 65°C while blowing in air and stirred for 48 hours. After that, the temperature of the flask was cooled, and 260.4g of methanol and 16.3g of 35% hydrochloric acid were added dropwise. The precipitated crystals were then separated into solid and liquid to obtain 107.7g of brown crystals.

[0083] The above brown crystals were confirmed to be a mixture of the following compound (101) and compound (101X).

[0084] [ka]

[0085] [ka]

[0086] A 500 mL four-neck flask was charged with 107.7 g of the brown crystals (a mixture of compounds (101) and (101X)), 281.2 g of xylene, and 25.1 g (0.50 mol) of hydrazine monohydrate, and the mixture was reacted at about 70°C for 3 hours while stirring under a nitrogen flow. The mixture was then washed with water and azeotropically dehydrated, and then filtered. The filtrate was cooled and seed crystals were added to perform crystallization, and solid-liquid separation was performed to obtain 82.1 g (yield 63.3%) of slightly orange crystals. The slightly orange crystals were1 Analysis by H-NMR and IR confirmed that the compound was the compound represented by the above chemical formula (101) (hereinafter, also referred to as "Bis-Bz-OPP"). The melting point of compound (101) (Bis-Bz-OPP) was 149 to 151°C, and the refractive index was 1.676. The results of the IR analysis of compound (101) are shown in Figure 1. 1 The results of H-NMR analysis are shown below.

[0087] Compound (101): 1 H-NMR (400MHz, CDCl3): σ7.50-7.26(m, 24H), σ5.25(s, 2H), σ4.08(s, 4H)

[0088] [Example 2] The same procedure as in Example 1 was carried out, except that Bz-OPP in Example 1 was replaced with 137.2 g (0.50 mol) of St-OPP. As a result, 70.4 g (yield 51.5%) of orange crystals were obtained. 1 Analysis by H-NMR and IR confirmed that the compound was a compound represented by chemical formula (102) (hereinafter, also referred to as "Bis-St-OPP"). The refractive index of compound (102) (Bis-St-OPP) was 1.663. The results of the IR analysis of compound (102) are shown in FIG. 2. 1 The results of H-NMR analysis are shown below.

[0089] [ka]

[0090] Compound (102): 1 H-NMR (400MHz, CDCl3): σ7.51-7.17(m, 24H),σ5.21(s, 2H),σ4.59-4.54(q, 2H),σ1.70-1.68(d, 6H)

[0091] [Example 3] The same procedure as in Example 1 was carried out, except that Bz-OPP in Example 1 was replaced with 126.2 g (0.50 mol) of CPP. As a result, 86.3 g (yield 68.7%) of white crystals were obtained. 1 Analysis by H-NMR and IR confirmed that the compound was a compound represented by chemical formula (103) (hereinafter, also referred to as "Bis-CPP"). The melting point of compound (103) (Bis-CPP) was 173 to 176°C, and the refractive index was 1.640. The IR analysis result of compound (103) is shown in FIG. 3. 1 The results of H-NMR analysis are shown below.

[0092] [ka]

[0093] Compound (103): 1 H-NMR (400MHz, CDCl3): σ8.13(s, 2H),σ7.54-7.17(m, 14H),σ3.02-2.97(m, 2H),σ1.81-1.69(m, 10H),σ1.51-1.26(m, 10H)

[0094] [Example 4] A 100 mL four-neck flask was charged with 15.0 (0.060 mol) of CPP, 15.0 g of toluene, and 1.5 g of methanesulfonic acid, and the mixture was heated to 90°C while stirring under a nitrogen flow. 0.81 g (0.027 mol) of 94% paraformaldehyde was added in small amounts over 1 hour and stirred for 3 hours. The temperature of the flask was then cooled, and the precipitated crystals were separated into solid and liquid to obtain 7.2 g of white crystals. The obtained crystals were dissolved in 19.0 g of xylene, washed with water, dehydrated by azeotropy, and then filtered. The filtrate was cooled and seed crystals were added to perform crystallization, and solid-liquid separation was performed to obtain 6.2 g of white crystals (yield 40.0%, paraformaldehyde equivalent). These white crystals were 1Analysis by H-NMR and IR confirmed that the compound was a compound represented by chemical formula (104) (hereinafter, also referred to as "Bis-CPP-F"). The melting point of compound (104) (Bis-CPP-F) was 129-134°C, and the refractive index was 1.622. The IR analysis result of compound (104) is shown in FIG. 4. 1 The results of H-NMR analysis are shown below.

[0095] [ka]

[0096] Compound (104): 1 H-NMR(400MHz, CDCl3): σ7.48-7.29(m, 10H),σ7.07-7.07(d, 2H),σ6.89-6.89(d, 2H),σ5.14(s, 2H), σ3.90(s, 2H),σ2.96-2.90(m, 2H),σ1.95-1.74(m, 10H),σ1.50-1.22(m, 10H)

[0097] [Example 5] A 100 mL four-neck flask was charged with 5.2 g (0.010 mol) of the compound Bis-Bz-OPP, 26.0 g of acetone, 1.8 g (0.021 mol) of 48% sodium hydroxide, and 0.10 g of benzyltrimethylammonium chloride, and the mixture was stirred under a nitrogen flow and heated to 55°C. 3.1 g (0.040 mol) of allyl chloride was added dropwise over 2 hours. The reaction was then carried out for 5 hours. After the excess allyl chloride was distilled off, 17.2 g of xylene was added, washed with water, dehydrated by azeotropy, and filtered. The filtrate was cooled and seed crystals were added to carry out crystallization, and solid-liquid separation was carried out to obtain 3.6 g of white crystals (yield 60.1%). These white crystals were 1 When analyzed by H-NMR and IR, it was confirmed that the compound was represented by chemical formula (111). The melting point of compound (111) was 148 to 152°C, and the refractive index was 1.640. The IR analysis result of compound (111) is shown in FIG. 5. 1 The results of H-NMR analysis are shown below.

[0098] [ka]

[0099] Compound (111): 1 H-NMR (400MHz, CDCl3): σ7.61-7.16(m, 24H),σ5.73-5.63(m, 2H),σ5.06-5.01(m, 4H),σ4.11(s, 4H),σ3.78-3.76(m, 4H)

[0100] [Example 6] The same procedure as in Example 5 was carried out, except that Bis-Bz-OPP in Example 5 was replaced with 5.5 g (0.010 mol) of Bis-St-OPP. As a result, 6.2 g (yield 98.9%) of an orange liquid was obtained. The orange crystals were 1 When analyzed by H-NMR and IR, it was confirmed that the compound was represented by chemical formula (112). The refractive index of compound (112) was 1.620. The IR analysis result of compound (112) is shown in FIG. 6. 1 The results of H-NMR analysis are shown below.

[0101] [ka]

[0102] Compound (112): 1 H-NMR(400MHz, CDCl3): σ7.61-7.14(m, 24H),σ5.70-5.60(m, 2H),σ5.04-4.99(m, 4H),σ4.73-4.66(q, 2H),σ3.77-3.55(m, 4H),σ1.68-1.66(d, 6H)

[0103] [Example 7] The same procedure as in Example 5 was carried out, except that Bis-CPP (5.0 g, 0.010 mol) was used instead of Bis-Bz-OPP. As a result, 3.8 g of white crystals (yield 65.2%) were obtained. 1 When analyzed by H-NMR and IR, it was confirmed that the compound was represented by chemical formula (113). The melting point of compound (113) was 210 to 212°C, and the refractive index was 1.613. The IR analysis result of compound (113) is shown in FIG. 7. 1 The results of H-NMR analysis are shown below.

[0104] [ka]

[0105] Compound (113): 1 H-NMR(400MHz, CDCl3): σ7.64-7.32(m, 14H),σ5.84-5.74(m, 2H),σ5.18-5.08(m, 4H),σ3.93-3. 91 (m, 4H), σ3.11-3.05 (m, 2H), σ1.92-1.75 (m, 10H), σ1.56-1.29 (m, 10H)

[0106] [Example 8] A 100 mL four-neck flask was charged with 5.2 g (0.010 mol) of the compound Bis-Bz-OPP, 7.4 g (0.16 mol) of epichlorohydrin, and 0.090 g of benzyltrimethylammonium chloride, and stirred under nitrogen flow, heated to 100 ° C, and stirred for 3 hours. After that, excess epichlorohydrin was distilled off, and 10.0 g of toluene was added, and 3.6 g (0.043 mol) of 48% sodium hydroxide was added dropwise at a kettle temperature of 100 ° C, and stirred for 9 hours. Then, 7.5 g of toluene was added, washed with water, and filtered after azeotropic dehydration. The filtrate was cooled and seed crystals were added to perform crystallization, and solid-liquid separation was performed to obtain 4.5 g of white crystals (yield 71.4%). The white crystals were 1When analyzed by H-NMR and IR, it was confirmed that the compound was represented by chemical formula (121). The melting point of compound (121) was 134 to 138°C, and the refractive index was 1.647. The IR analysis result of compound (121) is shown in Figure 8. 1 The results of H-NMR analysis are shown below.

[0107] [ka]

[0108] Compound (121): 1 H-NMR(400MHz, CDCl3): σ7.60-7.17(m, 24H),σ4.17-4.09(q, 4H),σ3.41-3.30(m, 4H),σ2.91-2.87(m, 2H),σ2.63-2.61(q, 2H),σ2.29-2.27(q, 2H)

[0109] [Example 9] The same procedure as in Example 8 was carried out, except that Bis-Bz-OPP was replaced with 5.0 g (0.010 mol) of Bis-CPP. As a result, 5.3 g (yield 86.2%) of white crystals were obtained. 1 When analyzed by H-NMR and IR, it was confirmed that the compound was represented by chemical formula (123). The melting point of compound (123) was 211 to 215°C, and the refractive index was 1.616. The IR analysis result of compound (123) is shown in Figure 9. 1 The results of H-NMR analysis are shown below.

[0110] [ka]

[0111] Compound (123): 1H-NMR(400MHz, CDCl3): σ7.62-7.34(m, 14H),σ3.50-3.49(q, 4H),σ3.12-2.98(m, 4H),σ2.70-2. 67(m, 2H),σ2.38-2.36(m, 2H),σ1.89-1.77(m, 10H),σ1.53-1.31(m, 10H)

[0112] [Example 10] A 100 mL four-neck flask was charged with 5.2 g (0.010 mol) of the compound Bis-Bz-OPP, 1.9 g (0.022 mol) of ethylene carbonate, 0.26 g of sodium carbonate, and 5.2 g of dimethylacetamide, and the mixture was stirred under a nitrogen flow while heating to 155°C and stirring for 16 hours. The temperature of the flask was then cooled to 100°C, and filtration was performed. 15.0 g of methanol was added to the filtrate to precipitate crystals. The precipitated crystals were separated into solid and liquid to obtain 4.4 g of white crude crystals. The obtained crude crystals and 8.8 g of toluene were charged, and the mixture was heated to 115°C while stirring under a nitrogen flow to dissolve the crystals. Then, seed crystals were added while cooling the flask temperature to perform crystallization, and solid-liquid separation was performed to obtain 3.2 g of white crystals (yield 52.7%). The white crystals were 1 When analyzed by H-NMR and IR, it was confirmed that the compound was represented by chemical formula (151). The melting point of compound (151) was 183 to 187°C, and the refractive index was 1.650. The IR analysis result of compound (151) is shown in Figure 10. 1 The results of H-NMR analysis are shown below.

[0113] [ka]

[0114] Compound (151): 1 H-NMR (400MHz, CDCl3): σ7.58-7.18(m, 24H),σ4.13(s, 4H),σ3.51-3.40(m, 8H),σ1.46-1.43(m, 2H)

[0115] [Example 11] The same procedure as in Example 10 was carried out, except that Bis-Bz-OPP in Example 10 was changed to 5.5 g (0.010 mol) of Bis-St-OPP. As a result, 2.4 g (yield 37.8%) of white crystals were obtained. 1 When analyzed by H-NMR and IR, it was confirmed that the compound was represented by chemical formula (152). The melting point of compound (152) was 167 to 173°C, and the refractive index was 1.640. The IR analysis result of compound (152) is shown in Figure 11. 1 The results of H-NMR analysis are shown below.

[0116] [ka]

[0117] Compound (152): 1 H-NMR (400MHz, CDCl3): σ7.57-7.16(m, 24H),σ4.71-4.65(q, 2H),σ3.49-3.39(m, 8H),σ3.32-3.26(m, 2H),σ1.70-1.67(q, 6H)

[0118] [Example 12] The same procedure as in Example 10 was carried out, except that Bis-Bz-OPP in Example 10 was changed to 10.1 g (0.020 mol) of Bis-CPP. As a result, 10.0 g (yield 84.6%) of white crystals were obtained. 1 When analyzed by H-NMR and IR, it was confirmed that the compound was represented by chemical formula (153). The melting point of compound (153) was 225 to 228°C, and the refractive index was 1.620. The IR analysis result of compound (153) is shown in FIG. 12. 1 The results of H-NMR analysis are shown below.

[0119] [ka]

[0120] Compound (153): 1 H-NMR (400MHz, CDCl3): σ7.61-7.36(m, 14H),σ3.60-3.55(m, 8H),σ3.08-3.01(m, 2H),σ1.93-1.77(m, 10H),σ1.59-1.30(m, 12H)

[0121] [Example 13] The same procedure as in Example 10 was carried out, except that Bis-Bz-OPP in Example 10 was changed to 4.0 g (0.0077 mol) of Bis-CPP-F. As a result, 2.9 g (yield 62.2%) of white crystals were obtained. 1 When analyzed by H-NMR and IR, it was confirmed that the compound was represented by chemical formula (154). The melting point of compound (154) was 74 to 79°C, and the refractive index was 1.603. The IR analysis result of compound (154) is shown in Figure 13. 1 The results of H-NMR analysis are shown below.

[0122] [ka] It was confirmed that.

[0123] Compound (154): 1 H-NMR(400MHz, CDCl3): σ7.52-7.31(m, 10H),σ7.12-7.11(d, 2H),σ7.00-6.99(d, 2H),σ3.96(s, 2H),σ3 .58-3.51(m, 8H),σ3.00-2.98(m, 2H),σ1.86-1.76(m, 10H),σ1.57-1.41(m, 12H)

[0124] [Example 14] In a 100 mL four-neck flask, 2.0 g (0.0039 mol) of the compound Bis-Bz-OPP, 1.3 g (0.013 mol), 40.0 g of dimethylacetamide, and 0.0010 g of p-methoxyphenol were charged and dissolved, then cooled to 5°C, and 1.2 g (0.013 mol) of acrylic acid chloride was added dropwise over 1 hour. Then, the mixture was stirred for 2 hours. The reaction solution was added dropwise to 100.0 g of purified water to precipitate crystals. Solid-liquid separation was performed to obtain 1.6 g of white crude crystals. The obtained crude crystals and 12.0 g of dimethylacetamide were charged, and the mixture was heated to 85°C while stirring under a nitrogen flow to dissolve the crystals. After filtration, seed crystals were added to the filtrate while cooling it to perform crystallization, and solid-liquid separation was performed to obtain 0.40 g of white crystals (yield 16.4%). The white crystals were 1 When analyzed by H-NMR and IR, it was confirmed that the compound was represented by chemical formula (131). The melting point of compound (131) was 165 to 172°C, and the refractive index was 1.645. The IR analysis result of compound (131) is shown in Figure 14. 1 The results of H-NMR analysis are shown below.

[0125] [ka]

[0126] Compound (131): 1 H-NMR (400MHz, CDCl3): σ7.44-7.19(m, 24H),σ6.38-6.33(q, 2H),σ6.11-6.04(q, 2H),σ5.86-5.83(q, 2H),σ3.94(s, 4H)

[0127] [Example 15] In a 100 mL four-neck flask, 2.0 g (0.0039 mol) of the compound Bis-Bz-OPP, 1.3 g (0.013 mol), 40.0 g of dimethylacetamide, and 0.0010 g of p-methoxyphenol were charged and dissolved, then cooled to 5°C, and 1.4 g (0.013 mol) of methacrylic acid chloride was added dropwise over 1 hour. After that, the mixture was stirred for 4 hours. The reaction liquid was dropped into 100.0 g of purified water to precipitate crystals. Solid-liquid separation was performed to obtain 1.4 g of white crude crystals. The obtained crude crystals and 2.4 g of xylene were charged, and the mixture was heated to 80°C while stirring under a nitrogen flow to dissolve the crystals. After filtration, seed crystals were added to the filtrate while cooling it to perform crystallization, and solid-liquid separation was performed to obtain 0.30 g of white crystals (yield 11.8%). These white crystals were 1 When analyzed by H-NMR and IR, it was confirmed that the compound was represented by chemical formula (141). The melting point of compound (141) was 168 to 174°C, and the refractive index was 1.633. The IR analysis result of compound (141) is shown in Figure 15. 1 The results of H-NMR analysis are shown below.

[0128] [ka]

[0129] Compound (141): 1 H-NMR (400MHz, CDCl3): σ7.45-7.18(m, 24H),σ6.07(s, 2H),σ5.56-5.55(t, 2H),σ3.94(s, 4H),σ1.80(s, 6H)

[0130] [Example 16] In a 100 mL four-neck flask, 3.0 g (0.0049 mol) of the compound synthesized in Example 10, 30.0 g of toluene, 0.30 g of methanesulfonic acid, 0.0020 g of p-methoxyphenol, and 1.0 g (0.14 mol) of acrylic acid were charged and stirred. The temperature was raised to 80° C., and the pressure in the flask was reduced to about 0.033 MPa, and stirring was performed for 7 hours while refluxing the toluene. 10.0 g of toluene was added to the reaction liquid, washed with water, azeotropically dehydrated, and then filtered. The toluene in the filtrate was distilled off and concentrated to obtain 3.4 g of a brown liquid (yield 97.1%). The white crystals were analyzed by HPLC, GPC, and IR, and it was confirmed that they were a composition consisting of a compound represented by chemical formula (161) and its polymer. The average molecular weight of compound (161) was 1218. The refractive index of compound (161) was 1.611. The IR analysis result of compound (161) is shown in FIG.

[0131] [ka]

[0132] [Comparative Example 1] 27.9g (0.15mol) of 4,4'-dihydroxybiphenyl, 29.1g (0.33mol) of ethylene carbonate, 1.4g of sodium carbonate, and 83.7g of dimethylacetamide were charged into a 200mL four-neck flask, and the mixture was stirred under nitrogen flow, heated to 155°C, and stirred for 8 hours. The temperature of the flask was then cooled to 110°C, and the mixture was filtered. The filtrate was cooled and seed crystals were added to perform crystallization, followed by solid-liquid separation to obtain 29.9g (72.7% yield) of white crystals of a compound represented by the following chemical formula (11). The melting point of the obtained compound (11) was 217-219°C, and the refractive index was 1.612.

[0133] [ka]

[0134] [Comparative Example 2] A 200 mL four-neck flask was charged with 30.0 g (0.15 mol) of bis(4-hydroxyphenyl)methane, 29.1 g (0.33 mol) of ethylene carbonate, 1.5 g of sodium carbonate, and 30.0 g of dimethylacetamide, and stirred under nitrogen flow, heated to 155 ° C, and stirred for 15 hours. The kettle temperature was cooled, and the reaction solution was added to 200.0 g of purified water to precipitate crystals. The precipitated crystals were separated into solid and liquid to obtain 42.8 g of white crude crystals. The obtained crude crystals and 150.0 g of 4-methyl-2-pentanone were charged, and the temperature was raised to 100 ° C while stirring under nitrogen flow to dissolve the crystals. After filtration, seed crystals were added to the filtrate while cooling it to perform crystallization, and solid-liquid separation was performed to obtain 30.6 g (yield 70.7%) of white crystals of a compound represented by the following chemical formula (12). The resulting compound (12) had a melting point of 109 to 111° C. and a refractive index of 1.579. [ka]

[0135] The refractive indices of the compounds synthesized in the Examples and Comparative Examples are summarized in Table 1 below.

[0136] [Table 1] Compound Refractive Index Example 1 1.676 Example 2 1.663 Example 3 1.640 Example 4 1.622 Example 5 1.640 Example 6 1.620 Example 7 1.613 Example 8 1.647 Example 9 1.616 Example 10 1.650 Example 11 1.640 Example 12 1.620 Example 13 1.603 Example 14 1.645 Example 15 1.633 Example 16 1.611 Comparative Example 1 1.612 Comparative Example 2 1.579

[0137] As described above, all of the compounds of the present invention synthesized (produced) in the examples were compounds having a polymerizable functional group. Furthermore, all of the compounds of the present invention synthesized (produced) in the examples showed high refractive indexes of 1.603 to 1.676 as shown in Table 1, and it was confirmed that they are suitable for optical resin materials and the like in which a high refractive index is desired.

[0138] The present invention can also be described as follows, but is not limited thereto.

[0139] (Appendix 1) A compound represented by the following chemical formula (1), a tautomer or stereoisomer thereof, or a salt thereof: [ka] In the above chemical formula (1), A is a single bond, a divalent hydrocarbon group, or a sulfonyl group, and one or more hydrogen atoms in the divalent hydrocarbon group are each independently optionally substituted with a methyl group or a phenyl group; R 1 and R 2 each represents a linear or alicyclic hydrocarbon group having 1 to 12 carbon atoms or an aralkyl group; R 1 and R 2 may be the same or different, X 1 and X 2 are each a hydrogen atom or a polymerizable functional group, and may be the same or different. (Appendix 2) In the formula (1), A is the divalent hydrocarbon group is a divalent chain hydrocarbon group or a divalent alicyclic hydrocarbon group, one or more hydrogen atoms in the divalent chain hydrocarbon group or the divalent alicyclic hydrocarbon group may each independently be substituted with a methyl group or a phenyl group; A compound according to appendix 1, a tautomer or stereoisomer thereof, or a salt thereof. (Appendix 3) In the above chemical formula (1), A is a single bond, a methylene group, or a cyclohexylene group, and a hydrogen atom in the methylene group may or may not be substituted with a methyl group or a phenyl group, R 1 and R 2 are respectively a cyclohexyl group, a benzyl group, or an α-methylbenzyl group; A compound according to appendix 1 or 2, a tautomer or stereoisomer thereof, or a salt thereof. (Appendix 4) In the above chemical formula (1), X 1 and X 2 are each a polymerizable functional group and may be the same or different from each other, A compound according to any one of claims 1 to 3, a tautomer or stereoisomer thereof, or a salt thereof. (Appendix 5) In the above chemical formula (1), X 1 and X 2 are each independently a substituent represented by any one of the groups represented by the following chemical formulas (2) to (5), or a tautomer or stereoisomer thereof, or a salt thereof, according to any one of claims 1 to 4. [ka] In the above chemical formula (2), * is a bond to the O atom in the chemical formula (1), n is an integer of 0 or 1. [ka] In the above chemical formula (3), * represents a bond to the O atom in the above chemical formula (1). [ka] In the chemical formula (4), * represents a bond to the O atom in the chemical formula (1), D is an ethylene or isopropylene group; m is an integer from 1 to 3; When there are multiple D's, each D may be the same or different. [ka] In the chemical formula (5), * represents a bond to the O atom in the chemical formula (1), E is an ethylene group or an isopropylene group; F is a hydrogen atom or a methyl group; l is an integer from 0 to 3; When there are multiple E's, each E may be the same or different. (Appendix 6) In the above chemical formula (1), A is a single bond, a methylene group, or a cyclohexylene group, and one or more hydrogen atoms of the methylene group may each independently be substituted with a methyl group or a phenyl group; A compound according to any one of appendixes 1 to 5, a tautomer or stereoisomer thereof, or a salt thereof. (Appendix 7) A refractive index enhancer comprising a compound according to any one of claims 1 to 6, a tautomer or stereoisomer thereof, or a salt thereof. (Appendix 8) A polymer of a monomer component comprising the compound according to any one of appendixes 1 to 6, a tautomer or stereoisomer thereof, or a salt thereof.

[0140] Although the present invention has been described above with reference to the embodiments and examples, the present invention is not limited to the above embodiments and examples. The configurations and details of the present invention can be arbitrarily and appropriately combined, modified, or selected as necessary without departing from the spirit of the present invention. [Industrial Applicability]

[0141] As described above, according to the present invention, it is possible to provide a compound, a refractive index enhancer, and a polymer capable of providing a resin material having a high refractive index. The use of the compound, the refractive index enhancer, and the polymer of the present invention is not particularly limited, and they can be used in a wide range of applications including general applications of high refractive index resin materials, and are of great industrial value.

Claims

1. A compound represented by the following chemical formula (1), a tautomer or stereoisomer thereof, or a salt thereof: 【Chemistry 1】 In the above chemical formula (1), A is a single bond, a divalent hydrocarbon group, or a sulfonyl group, and one or more hydrogen atoms in the divalent hydrocarbon group are each independently optionally substituted with a methyl group or a phenyl group; R １ and R ２ each represents a linear or alicyclic hydrocarbon group having 1 to 12 carbon atoms or an aralkyl group; R １ and R ２ may be the same or different, X １ and X ２ are each a hydrogen atom or a polymerizable functional group, and may be the same or different.

2. In the formula (1), A is the divalent hydrocarbon group is a divalent chain hydrocarbon group or a divalent alicyclic hydrocarbon group, one or more hydrogen atoms in the divalent chain hydrocarbon group or the divalent alicyclic hydrocarbon group may each independently be substituted with a methyl group or a phenyl group; 2. The compound according to claim 1, its tautomer or stereoisomer, or a salt thereof.

3. In the above chemical formula (1), A is a single bond, a methylene group, or a cyclohexylene group, and a hydrogen atom in the methylene group may or may not be substituted with a methyl group or a phenyl group, R １ and R ２ are each a cyclohexyl group, a benzyl group, or an α-methylbenzyl group; 2. The compound according to claim 1, its tautomer or stereoisomer, or a salt thereof.

4. In the above chemical formula (1), X １ and X ２ are each a polymerizable functional group and may be the same or different from each other, 2. The compound according to claim 1, its tautomer or stereoisomer, or a salt thereof.

5. In the above chemical formula (1), X １ and X ２ are each independently a substituent represented by any one of the groups represented by the following chemical formulas (2) to (5), or a tautomer or stereoisomer thereof, or a salt thereof, according to claim 1 : 【Chemistry 2】 In the above chemical formula (2), * is a bond to the O atom in the chemical formula (1), n is an integer of 0 or 1. 【Chemistry 3】 In the above chemical formula (3), * represents a bond to the O atom in the above chemical formula (1). 【Chemistry 4】 In the chemical formula (4), * represents a bond to the O atom in the chemical formula (1), D is an ethylene or isopropylene group; m is an integer from 1 to 3; When there are multiple D's, each D may be the same or different. 【Chemistry 5】 In the chemical formula (5), * represents a bond to the O atom in the chemical formula (1), E is an ethylene group or an isopropylene group; F is a hydrogen atom or a methyl group; l is an integer from 0 to 3; When there are multiple E's, each E may be the same or different.

6. In the above chemical formula (1), A is a single bond, a methylene group, or a cyclohexylene group, and one or more hydrogen atoms of the methylene group may each independently be substituted with a methyl group or a phenyl group; 2. The compound according to claim 1, its tautomer or stereoisomer, or a salt thereof.

7. A refractive index enhancer comprising the compound according to claim 1 , a tautomer or stereoisomer thereof, or a salt thereof.

8. A polymer of a monomer component comprising the compound according to any one of claims 1 to 6, a tautomer or stereoisomer thereof, or a salt thereof.

Images